Background

Following an assassination attempt that he foiled with his Thompson artistry, small-town political boss Leo O’Bannon summons his troops to his office. One of said troops, Hammett-esque anti-hero Tom Reagan (Gabriel Byrne) uses the opportunity to earn the ire of his boss by revealing his affair with Leo’s main squeeze, Verna (Marcia Gay Harden).

Stewing after watching his house burn down and now learning about the blatant betrayal of his closest acquaintances, Leo literally (and yes, I mean “literally”) kicks the insolent Tom out of his office and out of his club, set to the deliciously incongruous but strangely appropriate sound of tenor Frank Patterson crooning “Goodnight, Sweetheart” in the style of British vocalist Al Bowlly.

Thus, Leo evidently finds himself some decent clothes to wear while commanding his gangsters from the office above his nightclub. The timeless ensemble of a charcoal odd jacket and gray flannel trousers is dated perhaps only by the two-tone spectator wingtips… but they’re perhaps a better fit with this outfit than the slippers would have been!

Leo’s jacket has a welted breast pocket, flapped hip pockets on axis with the lowest two of his six-button front, and three-button cuffs. The jacket is tailored to give the burly Leo a more athletic silhouette, built up at the shoulders and suppressed at the waist with a half-belted back. A long single vent extends up the center back to the bottom of the belted waist line.

Leo takes a moment to consider his next move.

Leo wears a pale blue cotton shirt with widely spaced blue-gray stripes that alternate between thin double sets and a thicker single stripe. The shirt has a semi-spread collar, a large breast pocket, a plain front with mother-of-pearl buttons, and square single-button cuffs that Leo unbuttons and rolls up when he realizes he needs to kick some ass.

When your boss charges at you with rolled-up shirt sleeves and a stern expression, watch out. Be especially on guard if he’s surrounded by his gun-toting flunkies.

Leo’s maroon foulard tie has a subtle box pattern, styled apropos the era with a wide blade that ends at his high waistband. The knot is a small four-in-hand that looks less balanced with the wide blade.

Rather than a belt, Leo wears maroon box-patterned fabric suspenders that look like a larger scaled version of his tie pattern. The suspenders have shiny gold-toned adjusters and black leather ears that hook into buttons along the inside of his trouser waistband.

Leo delivers “the kiss-off.” You’re on your own now, Tom.

Leo’s gray flannel trousers have a long rise and double reverse pleats, consistent with menswear fads of the late ’20s and early ’30s. They have side pockets and a full fit through the hips and legs down to the turn-ups (cuffs) with a full break over his shoes.

The guy over Leo’s left shoulder attempts to pull off a similar look but hits a few bumps along his sartorial path.

Spectator shoes enjoyed the pinnacle of their popularity during the ’20s and ’30s, and it’s fitting that a confident if somewhat oblivious type like Leo O’Bannon would wear his when trying to command respect during a night of mob war. Leo’s medallion perforated semi-brogues have a black wingtip, black heel counter, and black lace panels on white vamps.

Flashy footwear doesn’t end with his shoes. Leo coordinates his socks to his shirt and tie with a pair of maroon socks with a solid blue stripe on each side and widely spaced brick red stripes providing a gentle tonal contrast.

Leo O’Bannon in colorfully-hosed respite.

On the third finger of his right hand, Leo wears a large gold ring with a round green setting, an appropriately colored stone for a guy who channels the luck o’ the Irish.

Unwelcome shoulder rubbing is not cool, Leo.

Having left his pocket watch to burn in the blazing house fire, Leo wears no watch at all in this sequence.

How to Get the Look

Leo O’Bannon’s conservatively dressed down office outfit could form the basis for your next date night attire, with a few updates here or there to make it contemporary for 2018… rather than 1928.